Inside: The Life of Dan Humphrey
by Jasmine LS
Summary: A story about Dan Humphrey, as Gossip Girl, as a writer, as a son, as a brother, as a lover. He meets again with Blair after that one night that made him fell for her, and things start building up again. An almost AU of Gossip Girl.
1. Dan Humphrey

Dan woke up at 6, finding himself stuck in yet again another girl's arms he barely knew. He untangled her from his torso and went to the bathroom, looking himself in the mirror. It was a routine as he took his toothbrush and toothpaste. He blankly watches himself as another day goes by and nothing really changes. Work, bar, one night stand, sleep and then it goes around. Working sounds like a trip but recycling the same hash of editing articles instead of actually making a journal of writing wasn't fascinating at all. But he's done being fascinating, he's done writing words that could destroy someone.

He searched for a shirt, and practically threw away the one suit he had at the back. He hasn't worn one since a dinner with a dean from Yale. He took the one shirt that was visible to him and a jacket. Pretty simple. He ignored the small voice at the back of his head yelling at his fashion sense. He heard the girl squirming on his bed and blinked her eyes at him.

"Morning," she said.

"Hey," he simply said.

"Listen, last night was…"

"I got to go," he immediately puts his shirt on and left the room, leaving the poor girl dumbfounded. He knows he's being an ass but this is New York and it is what it is. The girl said she was a New Yorker so this is the usual in New York.

Dan was off to work, but then his shoes seemed to be missing.

"You leaving?" asked the petite blonde who is none other than his own sister, Jenny.

"Yeah, I got another big day, as always," Dan said blankly while finding his shoes.

"Uh huh," Jenny replied, obviously rolling her eyes at him. "Will you be free this afternoon? I got th…"

"I'll tell dad you said hi," Dan smiled and Jenny could only smile back. Then she sees the poor girl inside of Dan's bedroom.

"Who's the babe?" Jenny said boringly.

"I…" he tried to remember but he was awfully wasted last night. Jessica? Amy? He puts in every Caucasian name he had known, but seems like he didn't really caught her name. He looked at Jenny, pleading. "Can you…?"

"I'll play the young ex-wife mode to send her away," Jenny poured some orange juice in the glass. "It's fortunate that we don't look alike." He always got his back by playing his 'scorned wife'. He sleeps around at night and in the morning; Jenny puts on a mask and feigned despair that her 'husband' is cheating on her. No one wants a cheating bastard.

"Yeah, I mean you get dad's charm off the bat," Dan searched around for his shoes.

"And you get mom's sarcasm," Jenny barked back. She watched as her brother searched for his shoes. "It's under the first shelf on the left." He always lost his shoes.

Dan smiled. "Thanks."

Jenny looked at him. "You know, next month I'll be moving out."

"Yeah you've told me that, weeks ago. That was the plan," Dan took his shoes off the shelf.

"You couldn't even find your own shoes without me. What makes you think it will be easy leaving you here alone? Plus, no one will be there to clean your tramps," she can't leave him. Not like this. Not when he's in the place where he needs company the most.

"Come on Jen. No cold feet," Dan laughed. "Besides, I pretty much raise you around here. Don't you think it should be me worrying about you out there on your own."

"Yeah well…"

"No cold feet," Dan cuts her. "The plan was for you to get out of here, take your butt to Manhattan, and show those Gucci snobs that you are a talented designer."

"And when are you going to Manhattan?" Jenny asked.

"The Spectator is basically in Manhattan," Dan sat down on the couch.

"Editing pictures in a tabloid mag doesn't seem like your dream," Jenny told him.

"Well, unlike you, I don't have a dream. Not anymore anyway," Dan smiled but Jenny could only look at him sadly. He used to have goals but he threw them away. "But I do have a wish. You. Achieving what you dream of. That is my wish. So no cold feet Jen. We'll be fine. Dad will be proud of you."

Jenny laughed at the last statement. "If only he understands what I am pursuing."

"He does. In his way," Dan looked straight into her eyes. Jenny heard the girl in Dan's bedroom squirming. He can do much better than sluts.

"You're 27 Dan. I think you should, I don't know, consider settling down." Jenny looked at him, obviously worried.

"Getting married at 27 is young don't you think? It would end as fast as Kim Kardashian's marriage at that age," Dan puts on his shoes.

"The fact that you are referencing Kim Kardashian is pretty disturbing. No, I don't mean marriage, I meant a relationship. You finding a girl and settle for at least 3 months not a one night stand. You could get herpes," Jenny scrunched her nose.

Dan kissed his sister on the cheek. "That's why we have condoms, young one."

"Eww," Jenny looked on as her brother waved goodbye.

Jenny was worried, as always about her brother's criteria on living life. He used to be the fun one, the one who is responsible, the stable brother. But nowadays Dan just lived off like other guys would be if their life was so messed up. Dan still blames himself, always did. Jenny kept holding onto him, just in case one day he finally knock his senses and turn around. Or worse, when he finally explode and kills himself.

Dan walked down the street, looking for a cab. He ignored the lady waiting a few meters away. Although the lady did waited longer, this is New York, you got to steal a cab to be a true New Yorker. He deems himself as a nice guy, enough anyway. He whistled a cab which drove pass the lady and he wasn't really sorry. He entered the cab and told his destination. He looked outside and he chuckled remembering that one girl who would scold him for it.

"_Don't be such a child Humphrey. She had waited longer."_

And it was said that she was the snob. Dan shook his head, that memory should be erased.

Dan received a call and it was from Alessandra. He ignored the call. Alessandra had called him again and again but he kept rejecting. He was done writing.

He arrived in his office and there was a pile of pictures on his desk. He just sat down and stared at it. He works in a new tabloid company called The Spectator as a somewhat writer, packing in anything the photographers has and puts down caption on pictures. He was sarcastic as his sister said and that is exactly what the tabloid needs. He looks through the pictures, didn't know a single damn person on it. But he's smart enough to make s snide remarks on it.

"I don't understand how you can work like this" his co-worker Pete stood beside him. "Yet I have to say, you are pretty good at it."

"It pays the bill," Dan smiled.

"Well, it's better to be on Diana's good side today. She went in pretty early, and you know it's all cranky in Payneville if she's here early," Pete saw Dan's nonchalance about the subject. "But no, you are his golden boy around here. Everyone knows she loves you. It's only us the minions that are in danger." Pete peeked into the closed curtains of Diana's office. "You banged her right?"

"Pete, I told you from the start, I did not sleep with Diana, nor am I a favorite or anything. I just do the job well and she likes that I'm sarcastic," he would never tell the real reason Diana favored him or that she pays him 10 times than others get.

"Okay, it's just… what everyone says," Pete looked around. "Do you know she had a fling with one of the Archibald?"

"Who's the Archibald?" Dan roamed through the pictures.

"You work in a freaking tabloid magazine and you have no idea who the Archibald is?" Pete was shocked. More so when Dan shook his head when he asked if The Van Der Bilt ring any bell. "You have got to be kidding me. Are you living in some restricted area Kim Jong Un own where they have no internet?"

"I live in Brooklyn. So Manhattan people are kind of off my 'I care about them so much I have to know them' list," he looked down as he checked another photo. "But I know Kim Kardashian so that's one."

"Because Diana made you write a piece on her when she divorced, and now Kim favored you because you're the nice journalist," Pete rolled his eyes. He looked on Dan. "You have a freaking degree from Dartmouth and you had an article published in TIME. What are you doing here dude?"

Dan looked at Pete. "Sometimes it's better to sell these lies rather than the truth. Lies are entertaining while it lasts but the truth, it could be someone's daughter."

**5 years ago**

"Now this is the kind of stuff that I just detest," Noah Shapiro barked at the young 21 years old Dan Humphrey. "Lonely Boy finding happiness in Brooklyn, meet the girl of his dreams and somehow couldn't get her but time goes by and finally they belong together. Do you think this internship is a joke?"

Dan could only raise his brows. "You told me to write what I knew."

"I told you to write something decent," Noah shook his head. "Is this because I took your article on Steven Parker and published it in The Times? That made your name public!"

"He was a Dean in Dartmouth. It almost cost me to be dropped," Dan ignored Noah's publisher, Alessandra who chuckled on the subject. "And it wasn't at all finished."

"It already became a hit! Have some balls, Humphrey. That Dartmouth degree is not taking you anywhere without this internship. Now find me another story that is worth my time," Noah went back to his office, leaving Dan at his desk. Dan shrugged and rolled his eyes. He knew that, a Dartmouth degree is nothing compared to a recommendation letter from Noah Shapiro.

"You okay?" Alessandra approached him.

"Yeah," Dan looked up front and he receives a glare from her. "No."

"Well, for one, you have balls to go that far with him," Alessandra sat on his desk, looking down on him. "What happened? I thought you said Steven Parker deserved it. And that you are too much of a diamond for Dartmouth that anything you'll write would be fine, even how much of a scandal it may cause."

Dan looked down, feeling the guilt all over again. "He has a daughter, and she's only 13." Dan looked up at Alessandra. "How would you feel if suddenly at 13 you have negative things thrown at you because it was known to public that your father was a sexual offender?"

Alessandra looked at him. "You know when you first came in here, I thought you were very much like Noah. Ballsy, rough and will do anything to tear some people apart, the sole reason he hired you. But no." Dan looked down. Seems like she'll be giving negative comments. "Fortunately you still have a heart."

"Thanks. I guess," Dan said.

"By the way. I got some tips about a scandal in the Upper East Side," Alessandra said and Dan actually froze hearing that. "Interested?"

"I'll pass," he looked right at his computer. No way, not another UES.

"Well, I guess fashion scandal is never your forte," Alessandra teased him. Truthfully, Upper East Side is not his forte. "Listen, try not to piss him off, find a story, anything that is not Brooklyn boy vs the world." Dan looked down. Hearing he actually wrote something of that sort makes him embarrassed.

"Yeah, well, I'll find something," Dan looked back at the screen.

"Oh, what about that one story you wrote, that short story on an Upper East Side snob," Alessandra tried to recall. "Clair Carlyle?"

Dan could only laugh at that. "No." he said simply.

"Why not?"

"She hates me," he simply said.

Working hour was up and Dan walked home. He took his phone out. He dialed a number and called up his girlfriend.

"Hey, Vanessa," he smiled. He had been in a relationship with Vanessa fresh out of high school. He met her while he was waiting for Jenny after her Fashion Class in the Upper East Side, and there she was fighting for the rights of an old bar right on Broadway. She was strong and mesmerizing, exotic some would say but her heart is what kept him with her. "Yeah I just got off from Shapiro's office."

He was in a good time of his life now, even if Shapiro busted it a bit publishing his article without his consent, it did bring his name in TIME magazine. Everybody kept saying that his daughter would survive. He takes that into his head and tried to ignore the uneasy feeling inside.

He walked up to his loft and sees a visitor. It was Steven Parker, in all black and white lilies in his hand.

"Hello, Daniel," he said, face tired, obviously from the scrutinize of people. "Happy now?"

"What?"

"Are you happy?" Steven suddenly smirked. "Yes, I play a little with those students. But come on who has a happy marriage nowadays. Even Evelyn knows that!" Steven sees Dan silencing himself. "Oh right, you didn't know her name. Evelyn Parker, my daughter, who won't even look at me in the eye when the article was published, who hates me more than my wife does, who left yesterday hanging herself in her room because it was too much!"

Dan was shocked. So shocked that all he could do was stare at him, stare at the man who was too broken to realize his own fault.

"Are you blaming me for your decisions?" Dan looked at him, eyes cold, baring his soul. "I just wrote a simple truth about your decisions and you're putting it all on me? Sorry Parker, but I have nothing to do with this. Your daughter is dead because of you. You're only putting this on me because you can't accept that you are your own doing."

Steven Parker latched his fist on Dan's head and Dan felt blood flowing on his head. Dan felt that he deserved the punch. Whatever he said, it was too cruel, even if it was true, it was too cruel, something that is best to keep in. Steven kept hitting him and he couldn't feel pain because he deserved it. The last thing he remembered was his father running to him to stop Steven.

He woke up in a hospital. He knew the smell well enough. His mother died in the same place when he was younger. He looked beside him and there was Vanessa sleeping on the couch. Then he looked at up front, there was the nurse checking his charts, scribbling things that he wouldn't be able to understand. He tried to get up when the nurse went out, but he had woken Vanessa up.

"Hey, hey, easy tiger," Vanessa helped him up. "He got you pretty bad, you almost broken a rib."

"Well, I hope I did," Dan looked down, laughing a bit.

"Hey, you okay?" Vanessa held his hand, hers was warm but then he felt that maybe he was the one who is too cold.

"No," Dan immediately answered. Suddenly his eyes watered. "How can I… I mean I should have known!"

"Hey, shh." Vanessa hugged him and tried to calm him down.

"Her name was Evelyn. And if I didn't write those things, no matter how true it was, she would still be in school, with her friends. And…."

"It's not your fault," she kept chanting, but it didn't work. As he kept on crying, for the guilt he had. He tried to give reasons that would help him get over it, but like what he said to Steven Parker, this is all his own doing and he's having the hardest time to avoid it. He's at fault, he killed that young girl.

"You told me before, that maybe the article was too mean, I was too frank," he calmed down a bit, but kept whispering to Vanessa. "Alessandra said I have a heart, I don't."

**Present**

From that moment, everything changed. He quits the internship in Shapiro's office but somehow miraculously finished his studies in Dartmouth. He loved Vanessa, he really did but somehow things didn't work out with him putting a distance with her or anyone around. The only person who could sort him out was his sister, Jenny. But even she had a hard time penetrating him.

Dan had told Pete about the Parker case. Hell everyone knew about it but despite of what Dan thinks, nobody actually blamed him. Steven Parker was an asshole himself so it was actually in his face that he screwed up. Dan sees it differently. He knew what he wrote, he knew what he had done that triggered Evelyn's suicide. His words, his thoughts were thrown into the article. It felt like he was the one who drove Evelyn into death. Words could kill.

And he hadn't wrote an attempted sentence of truth since then.

"She didn't die because of you, man," Pete looked at him.

"You would never know," Dan simply said.

"Dude, you have talent in writing. Not just this sarcastic comments about celebrities doing their riches but real writing," Pete said. "I would kill to have your talent." He said the wrong word. "No, I didn't mean that, you know… I mean I wanted…"

"I get it," Dan said. "But I'm done."

He's not.

"Daniel," he heard Diana calling him. "Office, now."

Dan walked into the office, ignoring the whispers around him. "Yeap?"

"Your old publisher Alessandra called me the other day," Diana eyed his reaction. When she sees none, she continued. "She wanted you to write for her client."

"Well, yeah, I'm kind of over writing," Dan said. Diana looked at him skeptically. "I rejected her a few times so she should understand."

"That particular client is actually one of my very good friend," Diana smiled. "Celia Rhodes, or sometimes people call her Cece. And she actually told me what she was looking for in a writer."

"What? People that can bullshit into their biography?" Dan tried.

"No. People who can see more than just a scandalous story. Cece wants her own story to be told out there but people kept judging her for her status. She needed someone who sees more. I think you are the perfect person to do that." Diana eyed him as Dan struggled for words.

"You know I don't write anymore," Dan said.

"Well I think you should start again," Diana looked straight into his eyes.

"Diana, I gave you pretty much all the stories in this magazines. I think that is enough of writing for you," Dan said.

"You think you are selling lies here by controlling the things coming out from the tabloid, but I think that was just you being selfish on what to write. If you say it was because of Parker's case, I doubt it. If you were really troubled by Parker you already left the journal world. But here you are. Still trying to control the stories." Diana looked through her window, looking at the busy journalist trying to find stories. "Those writers out there, which I kept wondering why I hired them in the first place added unnecessary scandals most of the times, I preferred yours anyway."

"They weren't lies, I just tweaked a couple of tips," Dan said. The truth can hurt someone.

Diana looked at him. "It was an ambiguous approach. Naturally it's actually those kinds that the crowd loved. Pretty smart. But truthfully it won't take you anywhere and I know it drives you crazy. It wasn't a problem, but 4 years of Gossip Girl pretty much bury those judgmental self worthy bastard in you."

**2 years ago**

It was a new magazine at the time and Diana Payne was looking for a new fresh start for a tabloid. He was actually interviewing for the junior editor spot but Diana thinks he's too young.

"Is this a tabloid?" he asked.

"No, it is not," Diana looked at him. "The interview is done, you can g…"

"You want real news right? A real scandal," Dan started. "I, uh… I went to the Upper East Side school, St. Jude. And well, everyone there had a story to tell."

"I don't understand, Mr. Humphrey," Diana eyed him.

"I was on a writer's block and I figured I would write something out of being in the Upper East Side. But I had no resources. These people, the people you are trying to find out, each of them, they had something to say. Just like those students in St. Jude and Constance, everyone had a secret to tell. But they won't just to save face. Image is pretty important around those kids," Dan looked straight at Diana. "But there is this medium, a simple blog I put under the username Gossip Girl. I linked it to several girls I knew would have the scandalous views on everything, reciting, 'You can use my name to reveal anything you wanted'. And they simply emailed Gossip Girl, telling all the scandal about Manhattan's elite. They'd do it because they will remain anonymous."

Diana listened to him very carefully. "What is the difference to other blogs that have tips like Perez Hilton?"

"They felt safer with the person who is also anonymous. Ambiguity works much better with them. Unlike Perez Hilton who searches for tips, Gossip Girl receives tips almost every day."

"And then you post those tips online?" Diana asked.

"No," Dan said and he sees Diana confused. "I get to decide their story. The tips are more than just scandals, they are sometimes a feeling, a confession. For 4 years, I prepared a medium where people tell their stories and I wrote them in a way I wanted. I think you wanted to write like that, you wanted the power to information and I can give you that. I can code in a new blog and send it to the people that will share information."

"Will you write then?" Diana asked him.

Dan was startled. "No. I will be an informer." Dan looked at her. "I don't write, not anymore anyway."

"Why?" Diana was curious. Dan just stayed silent. Diana eyed him. "What do you want in exchange?"

Dan smiled. "A job with a paycheck way too big for that job. Just so I can keep being undercover." Dan looked at her. "And I get to choose what to take from the blog."

Diana thought for a bit. She stood up and held her hand up. "Welcome to The Spectator Mr. Humphrey."

**Present**

"Listen, Diana…"

"I think you are smart enough to know that it was her father that drove her into suicide. You never felt guilty about the article," Diana smiled. "But you are afraid of the person who wrote that article. Cold, and mean. The kind of person you detested. You had the full power to control the story around here but you let others write it because you were afraid of that 21 years old Dan Humphrey. "

Dan looks at Diana. She knows him too well. "Well, what do you want me to say here?"

"Meet her today at the Oak Room for dinner. Wear a suit, and you don't have to decide now. See her first, and maybe she would change your mind," Diana smiled at him. "Trust me Daniel. This will be good for you. You think Evelyn Parker is haunting you. I think it's just you not realizing your real potential."

"What potential is that?" he asked.

"Writing," she smiled. "Plus once in a while I would like the information not to be tweaked around here. It will be interesting to see what people react to something real. You need to grow up Daniel. And stop controlling things, you are not Gossip Girl anymore."

"Please don't say that out loud," Dan covered his face. He looked at Diana. "Fine, I'll meet Celia Rhodes."

"Great!" Diana was pleased. "You would love her, she is an exceptional women."

Dan left work at 3, with Pete nagging him that he did bang Diana. Dan ignored him and went straight out. He bumped into someone and he recognized him. From school.

"Sorry," he said. Dan swore he knew him from school, but the only people that stuck out in his memory from school are two girls, one he wished he would never see again.

Dan hailed a cab, but a man rushed through him. Karma works like a bitch. He looked up, it's not raining. It is only a few blocks away, so he walked. He looked up and saw the big ad board of the new L'Oreal campaign and it wasn't an unfamiliar face.

"Serena Van Der Woodsen," he smiled. He used to have a huge crush on her when he first entered high school but it ends with him just looking at her persona. She topped his blog every week, along with another girl. She ended up exactly where he thought she would be, the center of attention.

Dan arrived at the hospital, and waved at the nurse at the reception. "Hello, Agnes."

"Hello, Daniel. Isn't today Jenny's turn?" the old nurse asked.

"She got this thing and here I am," Dan smiled. He was welcomed warmly over here and sometimes he liked here more than his own office.

"Well, your father is in for his walk, you should wait for him in his room," Agnes checked her list.

"Can I join him? Jenny said she does that a lot," Dan said.

"Of course," Agnes took him to the park.

Dan stood by the entrance and he saw his dad. Rufus Humphrey sitting on a bench, watching God knows what. Rufus had an accident a couple of years ago and loses half of his brain function, leading him to not understanding speeches or gestures. He had therapy for almost a year now and it seems that he understands a bit at miracle times.

After graduation, Dan worked as an assistant in a newspaper room downtown but his boss there had lost his patience when Dan actually slept with the intern he's having an affair with. Dan got fired and started picking up jobs in Starbucks and restaurants. When Rufus had an accident, Dan had to get a real job and The Spectator came in. Honestly, he did want to leave the journalism world but in the end, it is a world he knows best and he needs to earn to pay the hospital bills and never let Jenny for get her dreams.

"Hey dad," he sat beside him and Rufus just looks at him blankly. "Sorry Jenny couldn't be here, she had this fashion thing. And here I am." Dan smiled. He hoped his dad somehow understands him. "You know today Diana, my boss throw me the biggest FU ever. Mind my language dad. But yeah. She told me I need to grow up from my blog in high school." Dan looked at his own hands. "I guess I'm still stuck in high school dad, where there are too much around me and I feel the need to control things and I don't know, perhaps write my own story. I was a nobody there and I guess I wanted to be someone, at least in my own world, I can control them."

Dan looked around and sees many care around him.

"I'm scared of myself dad," Dan admitted. "Evelyn Parker died and suddenly I was reminded that my words in that article may or may not have pushed her to death. But it doesn't matter anyway. I remembered my words and God it is absolutely the person I always hated."

Dan looked at his dad and Rufus had no reaction. Dan smiled. "Well at least you had mom. She was always there for you right. Practically kicking your ass every time you screw up. And even when she's sick, you kept by her side. I wish I had someone who could just hit me in the head whenever I screw up."

Dan was preparing to leave for the Oak Room. Had to buy a suit from Armani because Diana would flip if he wore the suit he had since high school. He had to admit, he looked dapper.

It was fancy, classy, extravagant, all the expensive words coming out. He didn't realize that tonight was a party until the waiter asked for his name. Surprisingly he's in the guest list. He didn't know anyone there, it was all Upper East Side vibe all over again and quite frankly, he hated that vibe. A vibe that makes you feel that you don't belong. He looked around and he sees some familiar faces from school but definitely the ones he hindered from meeting.

"Daniel Humphrey?" he looked back and see a pretty waitress asking for him.

"Yes?"

"Cece is waiting for you in the VIP room," she smiled.

"Sure," he followed the waitress. "VIP huh." He could never get used to this kind of luxury.

He entered a very much expensive area of the Oak Room. He sat down as the waitress call in for Cece. Suddenly, a pretty blonde came in, and he recognized her. The ad girl. Serena Van Der Woodsen. The pretty blonde who is always headlining his blog during high school.

"Hi?" she was confused as to why he was here.

"Hey," he kept it short.

"You are not one of Cece's boy toys or anything right?" Serena asked.

"No, he's not," an old lady in her 60's came out, glamorous as ever and looking at the resemblance between her and Serena, it was obvious that those two are related. "Hello, dear. How was Moscow?" She kissed Serena on her cheeks.

"It was fine," Serena chirped. "Even if Blair did not make it easy since her break up with Nate."

Dan recognized that name. He wished she wasn't here.

"Ah you must be Daniel," Cece noticed him. "Serena, this is my new writer for my own biography."

"Oh," Serena smiled at him. If he didn't stare too much on her short skirt, he might be able to realize she was flirting with her eyes.

"Um, actually…" Dan started.

"But Diana did tell you the deal," Cece watched him.

"Deal?" Dan was confused.

"You are on a 1 night trial. Sure Diana recommended you and Alessandra who is a very successful publisher also thinks highly of you, but I wouldn't let anyone interfere with my life until he met my own standards." Cece smiled as she sees a more confused Dan. "For a start, just enjoy the party first and I'll be down with you in a minute."

"You have your criteria?" Dan didn't want to do it, but this challenge from this lady made him doing things against his will. "I need to know my standards too."

"All the writers around kept selling me ambiguous persona of myself and even if it is endearing to hear how strong of a woman I am, I don't want that," Cece stood up and eyed Dan. "No bullshit." Cece left him in the room with Serena.

"Sorry. My grandma is kind of weird at times," she smiled. "Listen, just hang around and you'll see that she's not that bad." She pulled him out to the party, and as easy as she flows, she held onto him like she had known him forever.

Dan eyed Cece and she was like other Upper East Side royal, twinkling their eyes on everything their guest says but probably never honest about anything themselves. It was all business. He sighed. No bullshit his ass. Cece Rhodes is just another mogul who wanted attention through her biography. Serena's company was a pleasure though. He liked that she laughs easily even at his stupid puns. Her smile was as bright as her hair and she was as free as a wild child. He remembered everyone in Constance wanted to know more of her, and actually know more of her. She was the queen in his blog. Serena and….

"Blair!" Serena called and Dan looked behind him. Queen B. The devil herself had come. He could see her eyeing him and her fake smile approached as she kissed Serena on the cheek. "I was looking for you, where have you been?"

"I was with my dad for a bit before he goes back to Italy," Blair smiled. Dan remembered as all hell breaks loose when Harold Waldorf left Eleanor Waldorf for a male model. He wrote it as the disgrace of Queen B. But it didn't wear her down as she begins to stay on stronger. "And you bought a charity case Humphrey here, how nice."

Dan rolled his eyes. Of course, after almost 10 years, Blair Waldorf still acts like she hates him.

And that is a whole other story in Dan's life. Something that happened once but as significant it was in his life, it didn't feel like that to Blair.

**To Be Continued**

**So yeah, I tweaked things a bit with the same plot, and decided to do this with continuous chapters because I realized that the One shot I made was too short. But read it if you want some spoilers but things may have changed a bit from there.**

** s/10306159/1/Inside**


	2. Blair Waldorf

**10 years ago**

Dan waited anxiously for the principal in front of his office. He looked at his watch. Another 5 minutes had gone by and he was still waiting. Not that he waited that long but the anxiety was building up. He was up for a candidate to represent St. Jude, as the one to be having dinner with St. Jude's alumni, Michael Weatherby. He was up against Nathaniel Archibald; which made him realize that the school politics sucks. The representative is supposed to score higher than a 3.8. Nate hasn't even reached 3. But he was determined. The recommendation letter would ensure him a Darthmouth acceptance. Which is why he settled with persuasion by words; on paper or from his own voice.

"Mr. Humphrey," he heard the principal called. He smiled at him. "Congratulations, you'll be needing a suit tonight."

If he could jump, he would. Dan sat down, smiling at himself. He couldn't believe it but he was actually one step closer towards his dream college.

"Oh, Mr. Humphrey," the principal called him again. "You will be escorting the female representative too from Constance. We haven't had the slightest idea of whom, so wait down the common hall for her. She'll be there with Headmistress Queller and she will give you your itinerary."

Dan nodded. He thinks he had an idea of whom.

He was sitting in a hallway, waiting for the girl who was supposed to be his partner in meeting Michael Weatherby. Dan was glad at least his persistence won him over Nate Archibald. He knew the Archibald clan was the big family in the Upper East Side. Though he was strictly calm because he got the tip that the senior Archibald wasn't playing fair with the money invested in his company that it didn't really benefit to be an Archibald at the time. He can't force that into his blog even if he had dozens of tips on them. There was no benefit to expose Howard Archibald if he still rolls the money from prison cell.

Though Dan did manage to put in vague news on them, which made up a small scandal that made being an Archibald sucked at the time.

Dan looked up. The unfairness of life always dawns at him and he felt that he had to work hard for everything. Even to scheme on some things. He didn't like it but he lived in the Upper East Side territory. It's hard to be in his shoes but he tried his best anyway. His mom always told him how nothing is hard, only your head deems to think the unlikely. Dan smiled. At least his life is leading well because nothing about controlling the Upper East side was hard. Everyone was very predictable. Except one person.

He heard footsteps coming in and he sees her and her preppy uniform. She has her business mode on and even if Dan barely knew her, he knew not to mess with her. Blair Waldorf struts down the hallway towards him, eyes looking at him but not really. Dan knew her persona, and quite frankly, he started to believe that it wasn't her persona, Blair is a bitch.

"Ugh, can you not smell like pork and cheese?" Blair whined while looking down on him.

"You must be Blair," he ignored her insults. "Where is Headmistress Queller?"

Blair sat beside him and he can smell her perfume. Cinnamon. Ironic for someone so bitter. "She has some guest in her office, should be here in a minute."

It was an awkward silence but it wasn't as if they were friends that they needed to speak to one another. Though Dan has this thing where when things are nerve wrecking, he talks.

"Congratulations on getting the spot," Dan said. Then he sees Blair smirking. "What?"

"I know what people think, Humphrey, I'm not dumb," Blair sighed as she crossed her legs.

"Okay," Dan was confused. "What do people think?"

Blair shook her head. "Obviously people think they would pick Serena. Not me. Sure she hasn't even pass the 3.8 gpa, but she's Sunshine Serena. Plus her dad is a famous doctor around with a mother that has crazy connections everywhere. Serena was a tough competitor obviously." Blair chuckled. Dan was surprised that was exactly his story with Nate. "I proved them wrong. I mean Serena might have been in a little trouble, but everything was fine."

He knew exactly what she meant. 2 weeks before he received a tip from Blair herself about Serena's admittance in the Ostroff Center which was why she had been missing classes. Obviously it caused a big scandal in the Upper East Side but like Nate's case, it was only a little trouble just to step closer into a dream.

"Wow," Dan said. He was about to silence himself but he had to say it. "You didn't prove me wrong though."

"What?" Blair looked at him.

"I.. uh, I kind of knew you'd get it," Dan said and Blair was now confused. "I mean yeah Serena is popular but, I guess people have better chances if they truly worked for it. You seem like the type of person who would, well, serve a girl to the devil to get something."

Blair rolled her eyes, now ignoring him. He didn't see her small smile though. He didn't mean it to be a compliment, or maybe he did.

Both stood up when they see Headmistress Queller walking towards them. She was in a hurry so she gave them their itinerary and some guidelines. They were left alone again and Dan just scanned the paper he had. The Oak Room. Then he realized he doesn't have a suit. "Shit, where am I going to find a suit at this hour?"

"Humphrey," Dan heard Blair calling him.

"You called me?" he was confused on why the stuck up girl called him.

"No, I called pork and cheese," she still has her feisty remarks. "I have checked on Michael Weatherby's background and, he's not so nice."

"I'm sorry, I don't get it," Dan looked at her. She didn't seem pleased either.

"Michael Weatherby is a man who is full of posh, money, greed and just a pain in the ass on the recommendation thing," Blair said. "But this dinner is a plus one, and even if he is an ass, he loves his wife dearly."

"So you're saying?" he wasn't understanding.

"He's a romantic, so he would love this gooey stuff," Blair talks like she was explaining everything. "Do you need me to say it?"

"Yes, because I don't understand anything you've said," Dan scratched his head. Blair took a deep breath.

"I don't want to do this but to get that recommendation letter, perhaps we should pair up and…" Blair took a deep breathe. "Play a couple."

"Excuse me?" now he was really confused on her proposals.

"I don't want to do this too but as individuals, he doesn't see us as anyone special but as a couple, we can get him emotionally. He's the sappy type so it should be quick a dinner tonight."

"I don't think playing a couple would make him giving us recommendation letter, Waldorf," Dan couldn't believe that Blair Waldorf was scheming all the way in. A scheme which doesn't make sense at all.

Blair rolled her eyes. "It would work. My plan never back fired!"

"Oh really," he said with much sarcasm.

"Listen, just one night of pretend. I know you want this as bad as I do. I know you've sent 300 essays to the Principal because an Archibald is your opponent," Blair looked at him in the eye. "Please."

Dan looked at her. She was right. Dan had made his own research on Michael Weatherby and he's not an easy guy. Only one got a recommendation letter before and that was because he was the minority and Michael Weatherby needed the good image at the time.

"Fine," he said and Blair almost jumps in joy. "But one condition."

"What kind of guy doesn't have a suit in his house?" Blair commented as the tailor took Dan's management on the pedestal.

"A normal guy?" Dan sighed. It wasn't his first answer.

"Don't be smart, Humphrey," Blair rolled her eyes. It wasn't her first eye rolling either.

Dan looked at the mirror. "Thanks anyway," he hated that he had to seek for her help.

Blair smiled. "Well, it's for my benefit as well. I don't want a hobo to escort me." Blair's insult has yet to end. "Plus, Armani is amazing. You can pay me back in 20 years."

"Haha, funny," Dan said. "Just so you know, those antique cars and Fenders in Brooklyn, it's not that cheap as well."

"What do you mean?"

"I mean while you love Giorgio, I love a fender, the classic one, not just any fender. We have different priorities here, Waldorf, so to mend my ego that you just punched, I'll be paying this suit with my money."

Blair shakes his head, but she respected that about him. If anything, he has his own pride to take care of.

"You do know I have no idea what a fender is," Blair said.

"Yeah, and I thought this guy here is Giorgio," Dan said.

It was almost 8 and he was already waiting in Café Boulud with Blair by his side. He had to admit she looked nice in her dress. He looked around and he sees a car pulling off, and Michael Weatherby was there and he wasn't alone. He brought his wife. Blair was right. That was one romantic old man there.

Immediately, Dan took Blair's hand and he sees a shocked Blair looking at him.

"What are you doing?" Blair hissed.

"Playing a couple," he whispered.

Both faked a smile when The Weatherbys approached them.

"Sorry, have we made you wait? I'm Patrice, Michael's wife," the wife asked and both young ones shook their heads. Patrice was very kind, and gentle. It didn't really match her husband's hard personality that everyone kept talking about. "Well, I'm sure you loved your company as well. Both of you make a lovely young couple."

"A couple?" Michael Weatherby asked. "I didn't know they were sending a couple this year."

"Dear, they are holding hands, what else could they be?" Patrice warned him.

"They didn't. It was a very pleasant surprise and achievement that we could get this opportunity," Dan said squeezing Blair's hand just to emphasis more. "Together. We're pretty low key."

"A pretty extravagant low key if you ask me," Blair added. "Let's go in."

The dinner went fantastic as Weatherby kept talking about him and his wife. Now Dan understood more. Michael was not the sappy one. His wife was and he mimics that personality out of her. He smiled. This was a good marriage. It's hard to find good marriage nowadays. Even if his own parents loved each other, it didn't erase the fact that Rufus did cheat once and Allison did ran away once. Michael and Patrice, they synched. Ironic since it was a planned marriage between the two.

"So, enough about us. How did you two love birds meet?" the wife asked them and they stood still. They haven't thought of a scenario.

"It was at school," Blair tried and she sees the wife kept looking at her, asking for more details.

"Oh come on, I want details," the wife seemed very eager. "I'm sorry, I love every love stories there is. I don't get my chances on young love when I was your age since my father had fated me to marry this guy here."

"Dear," Michael called in.

"Oh Michael, I have a perfect marriage and I am lucky to have you but that is the truth," his wife smiled at him. "We were arranged to be married and if it weren't you and me, we would have been divorced by now."

Dan realized that even if arranged marriage means you are settling down with a person you don't even know you would love, it doesn't mean that they were just settling. Michael and Patrice found love in a marriage and compared to all the love confessions of epic proportions the universe have, they found simple love, pure and simple love.

"Daniel, seems that your lady is rather embarrassed to tell. So man up here," Patrice jokingly flex her arms to show strength.

He's good at making up stories so he thought what the hell. Though he didn't realize he ended up telling the truth.

"I met this girl through an essay competition when we were both juniors," Dan started. It wasn't a lie, it was actually the first time he have encountered Blair Waldorf. Blair stared at him, a bit surprised. "I thought I had the best essay, the one who should win and honestly I went to see the ceremony just in spite of finding out who was this chick who did better than me. Then I see her receive her medal and all of the other students just cheered for her, and she had this poise when she came down the stage. But I guessed she looked lonely even with all her friends there and I don't know maybe because her parents weren't there. I know I was pissed when my mom had to miss all important events in my life since I was 12."

He stopped a bit and Blair sees himself calming down from something she barely knew.

"Blair was strong though. Unlike me who always bust himself in the bathroom crying, she just stood there, taking it all in and leave that darned sappy sad story behind her. And I thought," Dan looked at Blair. "And I thought I had to meet her." Though the reality was, he's Dan Humphrey and she's Blair Waldorf. A Humphrey does not just day hi to a Waldorf.

Dinner went well, and because of what Dan said, Michael Weatherby decided to write recommendation letter for both of them with Patrice's persuassion. Anyone could see the bright stars in Blair's eyes when he told her that. When the older couple excused themselves, Blair was left with Dan in front of the restaurant and suddenly, she hugged him out of joy.

"Easy kid," Dan patted her back as she jumped in his embrace. She stopped for a bit and looked at his eyes. Sincere and honest.

"Thank you," she slowly said. Dan was dumbfounded and he just nodded. She lets him go and started walking away from him while he just looks at her leaving. Wondering if there was something he had to do. But Blair stopped and looked back. "Why didn't you?"

"What?"

"You said you had to meet me. Why didn't you?" Blair looked at him, sincerely wanting answers.

"I.. uh. I was scared that you'll reject me," he somehow sees a glimmer of hope that she wouldn't that night. He walked slowly towards her, approaching her carefully. "I mean I am that guy everyone kept reminding that he's from Brooklyn. I smell like pork and cheese to you. And I…" If he was honest, he was always intrigued by her, which is why he ignored her most of the time. It would be too complicated and there was way too much differences between their lives. But tonight her doe eyes twinkled at him and he somehow felt dumb that he even considered not meeting her. She was the unpredictable one since even if he knew she was an Upper East Side princess who will never even link with people like him, he still sometimes feel that she could. It was always a stupid focus he had on her, but that night, it doesn't seem that stupid. Not at all.

"Well, you do smell like pork and cheese," Blair teased and they had to laugh about it. "I mean I don't know how I would react myself. My defense mode is pretty high back then and I think I would have shot you down immediately if you approached me."

Dan looked at her. "What about now?" Suddenly, he felt brave.

She looked up at his eyes. "What about it?"

"Would you meet me now if I approached you?" Dan asked.

She smiled a little. "Maybe."

He had to laugh a little at her sudden shyness. "Hi," he held his hand out. "I'm Dan Humphrey and I really liked your essay, even if my ego got scratched a bit that a girl beat me out."

Blair laughed. "I'm Blair Waldorf. It's nice to see such support from you, Humphrey."

"Um, I would love to take you to dinner but we just had one," Dan said out of his nervous tick and Blair just laughed. "So maybe, you would like to go watch Monsieur Hulot's Holiday?" He thought back for a moment and almost wanted to kick himself because not everyone knows Tati.

Blair smiled. "I do enjoy myself some Tati." Right then she became his favorite person in the Upper East Side.

**Present**

Dan let himself indulge in the open bar and never let his sight on Blair. Although it was pretty hard since she's practically in a backless dress and the fact that she kept glancing at him. What does she want anyway. It has been 10 years since they even talked and it wouldn't change because of one meeting. They had tons of meetings before, accidentally or not, and things never change.

Why would tonight be different?

Dan stared right across the room where Cece is, watching and studying her. She was nothing more than a socialite in his eyes now, but Diana kept pestering him that Cece had more inside of her. Though it was nice seeing her good relationship with her granddaughter since she hadn't been that good with her daughter. Dan knew of Lily Van Der Woodsen, and so far, Dan had one common thing with Cece; both have this dislike towards Lily.

Dan took another scotch and he sees Serena pulling Blair to the side. He was somehow confused with Serena's loyalty towards Blair. Blair had basically screwed her over many times in high school and she's still considering Blair as her best friend. He sees Blair pulling herself away from Serena and he regrets that he was watching when he saw her crying as she passed by. Maybe the alcohol kicked in or he really had lost his mind. He followed after her to the balcony and sees her looking at the New York City scene outside.

Dan took his suit off and gently puts it around her. She was surprised to see him there. "What are you doing?"

"Trust me, I have no idea," he tried not to stare at her as he stood beside her, facing the city. "It's a nice view."

Blair smirked. "Stop trying to make non-existent conversations, Humphrey."

"Sorry," he said with no sincere apology. He peeked down at her and he sees her mascara running down to her cheeks. She had been crying. "Come on, Waldorf. It's me. Just… talk."

Blair looked at him. "We haven't talked for years, Humphrey."

"That wasn't my fault," Dan had to for her sake, because even if he hates her guts to put up the walls around her when she's vulnerable, he needs to push through at times. Times when all she had was her pride. "You practically ignored me after graduation, and I'm sorry but that was on you."

Blair was still looking at him, searching for his eyes. "Do you hate me for it?"

Dan looked up, seeing her opening up. "You know I couldn't hate you."

"Not even now?" Blair stared at him.

"No," Dan almost whispered. "Not even now."

Blair stayed silent for a couple of second before being interrupted with the applause in the room behind them. Blair sighed as both watched Serena and Cece on stage with Cece pretty much beaming over her granddaughter. "That is Serena alright, always gets what she wants, what I want."

"What do you mean?" Dan was confused.

"I have a degree from Yale and I practically write better essays than Serena ever could. But I don't have a bright shiny blonde hair or a bright teeth when I smile, no sunshine Serena in me and they decided to give that position to Serena Van Der Woodsen," Blair looked at her best friend on the stage.

"Position?" Dan was slowly connecting.

"The Junior Editor in W magazine," Blair sighed. Seems like her tears had dried off. "I just, I mean she had to know her effect on others. Why would she take my chances? Why would she want what I wanted?" Blair suddenly looked at Dan and he didn't know what that look means.

Somehow it was switched now. Dan didn't understand why Blair was so loyal to Serena and he remembered clearly the reason Blair broke off with Chuck Bass in high school before was because the guy somewhat developed feelings for Serena, who is in fact her step sister. The incest in the Upper East Side really does blow his mind.

"You know something about Serena?" Dan asked. Blair looked at him. "Everyone may not have her luck but the thing is, she never knows about our hardship and hardship makes us human and… honestly, Serena might be a goddess but that is overrated anyway. Too many people putting her on a pedestal, that is not a good spot to be in. "

Blair looked at Dan.

"Come on Blair, if W doesn't want you, I'm pretty sure Vanity Fair or even Vogue would love to have you," Dan said. "You are a pretty good journalist yourself, and if W picks sunshine blondie rather than you, something is wrong with them."

Blair actually laughed at this. Dan knows a snide remark always gets her. Blair smiled, and for the first time, he felt that she might not hate him after all. "I've missed you, Humphrey."

Like the first time she hugged him, he was rather speechless. But he managed to say, "I've missed you too."

**10 years ago**

Dan waited in front of the movie booth for a show on nennete, the Orangutan. Blair was late and she wasn't picking up his calls. It wasn't as if they were seeing other but they basically liked the same movies and the same art. Might as well have someone like that in your life. Dan looked back and sees a frazzled Blair running towards him. Unlike the preppy and poise Upper East Side she always is, her hair was out of place and her breathing was uneven. He liked her best when she was like this, just being a normal girl that doesn't have her walls up.

"You are late," he raised his brows.

"I know. Don't rub it on my face Humphrey. I've got this thing," she handed him a paper bag, with a wrapped gift inside. Dan pulled it out and unwrap the gift, seeing it was the first edition of Fitzgerald's Tender is the Night. "Happy birthday Humphrey." He looks up and sees Blair smiling at him, genuinely and beautifully. "I know you clearly said that birthdays aren't exactly Humphrey tradition but I like birthdays and it is an important event."

Without realizing he approached her and had his palm on her cheeks and pulled her for a kiss, a mere peck. He knew he was falling for her because the day when he sees her peel her layers off, the deeper his feelings for her that he couldn't deny it anymore. He looked straight into her eyes and sees her smiling.

The first thing he thought was the political anarchy in the Upper East Side will not get in the way, he won't let it.

But school ends and somehow Blair went back to her side and he was forced to leave to his. Graduation came in and suddenly Blair decided that meeting her parents weren't a good idea and somehow left him bitter memories in his graduation day.

"I was just experimenting," she said. He knew she was lying. Even Blair Waldorf couldn't fake her way just for an experiment. But somehow this anarchy that the people have wouldn't let them be. And he tried to convince her otherwise but she ignores him. Which is why he left for Dartmouth and never look back. Though he never hated her, that is somehow a regret and a hope.

**Present**

Dan walked Blair back into her penthouse, the house that he had grown to remember one semester at school. "Still living like a princess I see." He had to say it, banter was part of their friendship. Blair laughed and he missed her genuine laugh.

"I live here alone now," Blair looked up to her building. "Dorota comes by from time to time just to fix me up with my regular routine so before you say it, yes, my house keeper still does most of the job. I do clean my wine glass perfectly fine though."

"Where's your mom?" he asked, and he remembered the scrutiny in her eyes every time he comes over.

"Somewhere in France, living a normal life with her new husband," Blair sighed and Dan searches for the hurt in her eyes and the fact that she beamed when she looked up, he sees none. "I miss her of course but I guess to have better relationship with me, she needs to be happy first and somehow with her right there, things between us just improved."

"Well, the fact that you openly said you missed her proved that," Dan smiled. "High school Blair Waldorf would never say that out loud."

Blair starred at him. "What about you? How's writing?"

Dan sighed and it is true that the brief moment they were together he basically told her every stories he had written but now, when things are entangling back, he had none for her.

"I'm working for a tabloid. I mean it's not anything inspiring but it pays," Dan looked down, embarrassed because between the two, he was much more ambitious than she was. Which says a lot. To be more ambitious than Blair Waldorf, you could in fact kill people to do it and he may have just done that.

Blair looked at him, somehow a question grows within her. "What happened?"

"Nothing," he didn't dare to look into her eyes. "Maybe that is the problem. Nothing much happened to me."

Silence interrupted them, and it wasn't comfortable because Blair looked like she had so many questions to ask. Dan hoped she doesn't go into it because at one point, he didn't want to have Blair be disappointed at him.

"Don't you have questions?" Blair suddenly asked which made him look up. "For me."

"Questions?"

"I did leave without any explanation and said it was all just an experiment…" she looked away.

"You had to go to Yale, to New Haven…"

"I had a plan since I was 13, and you weren't in it," she cuts him and he was left with a surprise. "If we'd continue whatever it is we had that time, I'll need to change my plans."

"What were your plans?" Dan asked slowly.

"Graduate the top in my class, Yale, being an editor in a fashion magazine, take over the world…" she was glad Dan laughed at the last part. "I'll get everything if I go according to plan."

"Why would me being in your life change your plans?" Dan asked. He didn't understand this.

She smiled. "Because in spite of all those pork and cheese smell and the fact that you're from Brooklyn, you were a wonderful companion and I know myself enough that if I kept hanging around you I would eventually find myself falling for you. You're the only guy I know who knows who Tati is and would debate about Degaz with me. How could anyone not like you?"

Dan stared at her, his head is spinning.

"But you dated that Archibald guy from high school," he hoped that was a fluke too.

"Nate was different. He was like every other guy," Blair smiled. "He was the guy I would not prioritize over my own goals." Blair's eyes watered and she looked at him. "I had to choose myself."

"That doesn't make any sense Blair," Dan was suddenly angry and hurt.

"Well it does to me," Blair looked down and pulled his suit off her shoulders to hand it back to him. "You may not understand this but I know myself and I need to stick to the plan."

"Blair…" Dan suddenly pleaded. He know what this is. If he lets her speak, she will go back to pretending that she hates him, that nothing would ever happen between them, like he was a taboo to her.

"It was nice talking to you," she steps back and pleaded with her eyes for his understanding. "I've missed you but this is where it should end, the good way. At least I know you don't hate me and that is a good feeling." She disappeared behind the doors and he was left alone yet again. He was back to where he was 10 years ago, when Blair left him again. This time though, he somehow knew for sure that Blair wanted him, like he had wanted her, but her believe in this plan and her believe in this idea of being a stereotype in the Upper East Side reflects her decisions and it is starting to piss him off.

He walked back to the party, right where The Oak Room stands and he sees Cece bidding goodbye to her guests. Cece saw him and smiled.

"I thought you would give up on the deal," Cece said.

"I'm here because I need to tell you something," Dan said. Firm on his two feet, he started. "I need to understand your world, Cece. I can't just type in a lie or the things that you think aren't BS because from what I see, anything from you is as good as anything from the people who judged you. So let me inside, I need to understand this society before I could carefully write about you. You want no bullshit right, so that is up to me to decide what bullshit is there. You roam around those people and you act like how they wanted and that is not going into the book because that is bullshit. I'll write once I see inside, and you are helping me with it."

Cece smiled and shakes her head. "Diana was right. You are something else." Cece has a phone in her hand and called a number. "Get me Gerrard, I need a new apartment set up for a bachelor here." She ended her call and looked at Dan, handed her hand. "Welcome to the Upper East Side, Daniel."

He wasn't watching anymore, he will live it, like an Upper East Side, right at the heart of it. He will show Blair that as much as the anarchy is important in the Upper East Side, anyone can tumble it down and it was also the point that Dan Humphrey started writing again.

**To Be Continued**

**Thank you for the follows and reviews, to the favorites as well. I guess in this chapter I wanted to show that Dan has that much power if he chose to use his writing skills well. He was neglecting his moral before for his ambitions and now when he has chosen a path, it will lead him into another route and hopefully to Blair as well. There will be more flashbacks in the next chapters on Dan and Blair with more present scenes with Dan and Serena to spice things up. Hope you enjoy!**


	3. Manhattan

Dan looked at his new apartment and sighed. He asked Cece to just cancel on the apartment because his loft was just fine but Cece insisted that he had to live inside the Upper East Side to understand it. He doubted it will make a difference but he did appreciate the nice view. He walked up to his new bedroom and he hates how empty it feels. His old room is filled with books and films and posters and arts while this is just white walls. He was allowed to at least decorate so he put it in his mind to complete the task when he is finished with the day.

He looked out the Manhattan sky and it didn't feel out of place. He knew the place well enough from high school and he knew the roads around, but he didn't feel like he knew the people at all. He wrote some stuff about them, secrets and scandals but he realized he never understood any of them. Maybe it was him being a cynic but then again it really didn't put him inside either. He was still just watching them and even if he wanted to be someone to those trust fund babies, he never felt like he wanted to be a part of them.

He remembered how Blair kept her pride as a resident in the Upper East Side but he never saw her as a trust fund baby even if she is, or as an Upper East Side princess which she is. Somehow when he got to know her, Blair was Blair. Until yesterday when she declared her plans and selfishness. Dan thought Blair had shown how truly rich her pocket but such poor judgments. He even thought that Blair never knew how to be happy that being happy scared her. He didn't know how to make her happy, but he do know staying inside her bubble was not doing well on the happy part.

He knew the real reason he accepted Cece's offer was because he needed to dig in more into Blair's life, and finally pulling her out of it. He hates the Upper East Side for stating such social standards in the fucking modern day. This is not a love story in the medieval era where rich girls don't marry poor boys, he is in fact not at all poor. Those lines between Manhattan and Brooklyn, they had to go.

Dan walked out of the apartment and he sees another guy, supposed to be his neighbor. He said a simple hey and the neighbor looked at him, where he found out it was Nathaniel Archibald. Great.

"Hey, you new." Nate walked up to him and Dan wanted to curse himself for being polite. Before he could answer, it seemed that Nate recognized him. "You were in St. Jude's right?" It was highly surprising that he remembered. "I uh, I think we had a few classes together and… You seemed surprised."

"Yeah, no one really remembers me," Dan was surprised. "You do and that is very surprising. In deed."

"Well, you dated Blair so…"

"Wait, you knew about that?" more surprised kept coming.

"Yeah, I mean I am also one of her exes now, and when we dated she talked about her exes and your name came up and so, I searched," Nate said with all honestly and naivety.

"You searched?" Dan eyed him.

"Yeah I mean I wasn't going around asking people of your address or anything, just a few background checks…"

"Background checks?" what is he, a mafia?

"Blair is a pretty hard catch, okay. I just wanted to see how the exes are doing and keeping my turf," Nate was honest and truthfully, out of all of the Upper East Side Constance and St. Jude's students, only Nate Archibald didn't send any tips to Gossip Girl. Dan thought maybe it was because of the scandal surrounding him but Blair who knew him since kid told Dan how Nate is as honest as he can be. Looking at the guy in front of him, that seems to be true.

"Well, she is a hard catch," Dan agreed. "I'm sorry but I don't really know you but I am new here so…" Dan puts his hand up. "Dan Humphrey."

Nate grabbed his hand. "Nate Archibald." It was the day Dan stopped referring him as the Archibald Guy. And that the hatred he had for Nate since high school seems really childish and naïve, as Nate was genuinely the nicest guy he had ever met, and perhaps the guy that leads him to understand the Upper East Side better and somehow, understand Blair better.

Dan had an appointment with Cece and her PR person, which he added as unnecessary since he wanted the story he writes to be exclusive and nothing to be censored by a PR person. Though Cece insisted that it is needed to bring out some of the truth out. Dan looks at it as just another thing to ignore.

Though it is really hard to ignore Serena Van Der Woodsen.

"She's your PR person?" Dan had to ask. "Your granddaughter?"

"Well yes. Serena knows me better than Lily does and she does know that I have boundaries. I know you want honest truth Mr. Humphrey , but I have a family. I hope you would understand that I still need to protect my family. Lily has done enough to destroy some dignity of this family and some others," Cece ignored Serena's shush but Dan agreed on that, absolutely. "But I have 2 grandchildren and who are young and have their whole future ahead and I think only Serena could put those boundaries around me."

Dan looked at Serena and he didn't understand the look on her face. But Cece had a point and he respect that she still believed in the hold for a family. Cece excused herself and left him with Serena.

"Fine," Dan said. He sees Serena smiling. "So what is the guidelines?"

"Excuse me?" Serena was confused.

"Guidelines, what are the things that aren't I or, we supposed to write?" Dan asked.

"Well, for one, my brother is in his third year now and I am hoping he's only focusing on that. There are a few incidents in this family that we ourselves regret so for one, nothing on Eric Van Der Woodsen. Even if grandma mentions him, I don't want him in that biography," Serena looked at him seriously.

"But if there were only you, people will start talking about favoritism," Dan said. He knows the society of gossip and he knows what people would say on some circumstances. "You would throw him into the spotlight just by not mentioning him. I could already see the magazines calling out your brother as the troubled grandchild beside her sister who is getting great jobs."

"Ok." She agreed. "But anything about Eric goes through me first."

"Sure," Dan was surprised of how protective Serena is to her brother. "What about your mom?"

"Well, I wouldn't want to scar her that bad but Cece is the grandmother here, I can't really do anything on what she wanted to reveal about my mom." But Serena's indifference with her mom was much more noticeable. Like Cece, Serena had it tough with the middle generation.

"What about you?" Dan asked.

"What?"

"What do you want to cover up about yourself," Dan looked at her.

"Well, I…" Serena was dumbfounded since no one really asked about her since her trademark was just stealing the attention, why cover it up. "I think people know me enough through tabloids so whatever Cece tells you might already be out there."

"I've only known Cece for like not even an hour accumulated but I do know that she loves you," Dan said, in all honesty. "What makes you think she would say the same thing about those tabloid does?"

"Well, I know she loves me but I don't think she trusts me," Serena looked down. "Anyway, anything about Eric will go through me first. Since Cece told me about it late, I couldn't figure out other guidelines but I guess we'll be seeing much of each other, Mr. Humphrey."

He liked her better when she was a bit tipsy. The Serena in front of him was just… aloof.

Serena excused herself and Dan had to say this. "Well, if it makes you feel better, just making you involved in her life time biography showed that she trusts you. I guess I wonder if you trust yourself."

"You don't know me," Serena looked back. The same thing Blair had said to him years ago.

"I don't but I am a good reader," Dan smiled. The irony was only Blair proved him wrong on that.

**10 years ago**

"This is totally unacceptable," Blair looked at Dan from head to toe. "Plaids and jeans to Boulud's. Do they sell death wishes too in Gap?"

"Blair, you said casual. This is casual," Dan said, trying not to laugh at Blair's own extravagance of dressing. It was just a normal dinner in somewhat a fancy restaurant in Manhattan. They get to their seats when Dan noticed her pearls. "Don't you think pearls are a bit too much for a simple dinner?"

"Well, I don't see why not," Blair ignored him and scanned the menu. So did he and he was a bit dumbfounded on the price. "I know this is a little expensive…" Blair started.

"Well, you do pay for the nice surrounding and the very shiny cutleries here," he was being sarcastic and she watched him, glared. "Okay I don't mean to be a Brooklyn brat, but I had to say it."

"I like fine things, and I don't see nothing wrong with that," she knew he would judge her. Obviously, it is what everyone out of Manhattan does to the Upper East Side.

"Well, we have that in common," Dan mindlessly scanned the menu for something that he would see as edible.

"What do you mean? You just put your judgment on me Humphrey," Blair watched him.

"Well, I can see why you like these fine things, and no pun intended, it is perfectly fine. I like plaids and whatever you say I will always like plaids. You may not notice but it is also perfectly fine to you too," Dan smiled and Blair could only watch him, always being surprised at how he replies.

"That is not fair," Blair blurted out.

"What is?" Dan was surprised.

"I seem like such an open book and here you are, surprising me every time we have a conversation." Blair looked down, a bit embarrassed. "I wanted to seem surprising to you too at times. You have no idea what those surprises could make me feel. And I wanted you to feel the same way."

With that Dan realized that even if he read Blair well, sometimes better than everyone else, she always surprises him, much more that she herself realizes. He never read her enough, as if he has so much to explore. Sometimes he realized he read her wrongly when she steps up and surprised him. The Blair who puts up wall of defenses had just honestly told him her deepest feelings, her deepest thoughts and he never knew he would be watching her and be mesmerized by it. It was like it could be never ending with Blair. He thought he could read her forever, being a bad reader was perfectly fine and just be surprised by her every single day.

Dan smiled and held her hand. "Well, if you don't realize this, I am already in too deep Blair. That's not fair to me that you could pull me in into this fancy restaurants and I still can't get you to watch Big League."

"You know I wouldn't be caught dead at a Big League Festival." Blair laughed a bit. She was cheeky and he liked that.

He didn't recognize the click of a phone that would make them split.

**Present**

"This is like living as a doll. Being all prepped and played," Dan looked at the mirror as the tailor fitted his new Armani suit on him. Cece smiled widely as she monitored him from the sofa near. "And you seem to have fun with it."

"Why aren't you?" Cece watched him roll his eyes. "You remember that to be cynical and judgmental is only allowed once you learn about this side of the borough."

"You're talking like it is such a different world," somehow he is regretting his decision. Maybe it is not such a good idea to officially enter this side of the world. He was brought in before in high school but he was focusing on school enough to not get sucked in. Now he is volunteering to be in. He wants to run away.

"It is no different, trust me. But it is somehow difficult the way we try to live," Cece took the champagne on the table for a sip. "I never understood half of what I do and the only reason I could think of was because I am an Upper East Side resident."

"At least you're starting with honesty now," Dan looked down as he was handed cufflinks. He wore them and turned towards Cece, head high. "Well, do I look Upper East Side Dapper?"

"Handsome," Cece walked up to him and brushed his shoulders. "I remembered your father well, quite handsome but I see how you take on your mother's side as well. And that is a good thing." Dan froze as he looked right at Cece. "Seeing your reaction means you knew quite well what I am talking about."

"You… knew about my dad and…"

"He's the lead singer and my daughter is the groupie. Yes I am aware that they have… mingled," Cece smiled as she looked to the mirror behind Dan. "I never liked him, but I do like your mother. And seems like it is good that you took your mother's side a lot. Even more than I liked my own daughter." Dan was now confused. He never knew Cece knew Allison as well. "Of course you didn't remember, you were too young."

"How did you know my mom?" Dan inquired.

"Well, surprisingly groupie love is kind of hard to forget and that your father met with my daughter again when you were about 10, went on an escapade to God knows where. I wasn't really keen on him and decided, well, let's start destroying the family," Cece could only laugh when she sees the terror in Dan's eyes. "At first." Cece walked back to the sofa. "Your mother was quite a charmer. I first met her when she was waiting for you and your sister from school and she didn't flinch even once when I approached her. I told her about her husband's infidelity but she took it like a strong woman would do to protect her children. She put in a smile for you and led a life that says it's okay to be broken some times. I wish I had that notion when I was her age."

"Well, she left for a while after that," Dan sat beside her. "She um, she left for Hudson to become an artist. It was for a week that turns into a summer and suddenly she came back with such sorry on her face, begging for my dad to forgive her and I guess, they do deserve each other at some point."

"Well, I don't know what happen to you boy, but has anyone told you how negative you are?" Cece watched him carefully.

"It was always cynical and judgmental. Could be the same acronym for it," Dan smiled.

"Do you hate your mother for leaving?" Cece asked.

"No, I mean she's my mom. I could never hate her. Before she got sick, I can understand how she needs to get out of our lives for a bit. In front of her was the man who cheated on her with a groupie in his one hit wonder band and I don't know, if it were me, I would have had to leave too," Dan said with no pity or sorry. "I guess even being as young as I was, I understand her leaving the house for a bit."

"You believed she would come back?" Cece asked.

"Yeah. Which is why it pissed me off when she just gave up to leukemia 2 years after," Dan looked down. "Out of all the people around me, I always thought my mom would come back for me, for Jenny no matter what but seems like the universe loved to screw me on those type of shit."

"You know she told me about this," Cece straightened his collar and tie. "She told me her oldest child would forgive her for anything because you were much more similar to her. Then she told me about how her 10 years old child would push her on her art, push her to never give up on her dreams just like she had told him and never even once asked her about his missing dad. I was always fascinated by Allison and also by you Daniel. When Diana told me about you, I had a feeling I would see Allison in you and in fact I did. She raised you well Daniel, very well in deed. Something that I haven't done well with my own daughter."

Dan smiled. "Well you raised your grand daughter well."

Cece smiled. "Talking about Serena, I have a favor to ask you."

It was a ball, or something. Dan didn't quite understand the concept quite yet. A cotillion was definitely something that he didn't understand, the fact that the families were in fact promoting their daughters to the hands of the men out there. Most of the girls were just in fact 16 and he didn't understand why they would even want to participate. He was in fact asked to escort Serena who is in charge of the seating arrangements. Since she was busy at her new work, she had no time to look for a date.

"You look dapper," Serena smiled and Dan looked at the champagne in her hands. Her aloof was partially gone. She had some issues on alcohol it seems. Dan tried not to judge. "I know Cece sent you here to monitor me, but I am fine."

"Well, her direct words was, 'You can learn a lot by hanging around Serena'. So yeah, I am here to learn about this debutante thing," Dan looked around and the young girls just squealed around each other waiting for their turns. "What is the purpose of this debutante thing?"

Serena looked at him and tried to say something. "Actually, that is a good question. I never really know." Serena giggled suddenly. She was definitely a bit tipsy. "You can't learn much from me. I mean I never really understand anything around here myself. Cece sent you here because she clearly likes you and wanted something to happen between us."

"Excuse me?"

"Well, she did the same thing with this other guy and of course we had a few dates afterwards but I don't know, those guys seems like they are not just my type. Sorry but so are you," Serena smiled. Definitely drunk honesty.

"It's a good thing you're not my type either," Dan retorted and somehow Serena seemed surprised about that. "Well, I just head over around to see the big buzz around this." He didn't realize that Serena's eyes suddenly changed.

"Wait," Serena pulled his arm. "You are here to escort me so escort me." Serena insisted that they move around the party with her arms around his and truthfully, he was glad for her company since he didn't know what else to do with a room full of strangers.

Then he realized something, not only the daughters were paraded but the sons too. Every time he spoke to someone, they were all glorifying how their sons would venture their business and are going to Ivy Leagues. Since Dan is from Dartmouth, some of the guys were looking up to him like a God and somehow, it felt good.

The bell rang and everyone's eyes were set on the staged stairs where the debutantes will walk down. Lights were dimmed and the focus was on the stage. Dan didn't move an inch or even budge a bit when he sees her walking down with her hands around another man's arm. Dan looked around and sees the front poster that says, "Hosted by Waldorf". So the cotillion was in fact all in favor for Blair and her mother's company.

"Ladies and Gentleman, I would like to thank you for coming today to our 63rd Annual Debutante Ball," Blair spoke smoothly through the microphone. Dan watched and this was all her, this thing that he never understood, being a debutante, everything was reflecting on her and he never gets this. It used to amuse him that he had a lot to learn about Blair but now it just sucks that he didn't understand this part of her. The part where social hierarchy was so important that she had to leave.

She looked down and she sees him. He knows she sees him. But she remained her poise and hosted the party. He can still feel Serena's arm linking with his and he can't lie, he hoped it hurt Blair a bit seeing them. He needs a reaction. He needs her to actually feel something here. He knows Blair's insecurities on Serena more than anyone and he hates himself for using it against her.

"Our final debutante…" finally, it is almost over. It would be time to mingle again and he didn't felt like mingling. After all, everything was just sucky for him.

"I'm gonna go," Dan whispered to Serena. But she pulled him.

"There is still the after party," Serena held him in his place. He looked at her, wondering why she is insisting so much. "Come on, I promise you, it would be fun. They have an open bar and there, you can see how these elitist don't seem much more extravagant than their clothes."

It is interesting to see that side. He had never been to an Upper East Side party before, he was never invited in high school. Even when he was with Blair, she herself insisted there wasn't anything to see at such party. The debutante exited and so does Blair. He found himself searching despite of all the things that had happened. But he was dragged by Serena, on to the place that he will have his first lesson in the Upper East Side.

No one hates drinking.

It was just like the usual high school party, there are booze (fine ones of course), loud music and probably someone fucking his girl upstairs. But this upstairs is a five star hotel Waldorf Astoria, which he find it very much like Blair to input anything that has her name on it. Dan asked for a scotch and Serena downs Martini.

"Don't you think you are done with that," Dan pulled her drink from her, which she took back. "You had a few champagnes already."

"No," she pointed her finger at him. "I never have bad hang overs so it is fine to drink too much." Serena giggled again. "I wish I have your life, Dan. You don't seem to have much problems. Me, I have a mother who never took care of me and my dad doesn't want me. Plus my grandma seems to think I'm trouble even if I always do everything to please her." She looked down. "I'm not Blair, I can't just do everything in passion. I never have her courage."

Then he sees the real Serena Van Der Woodsen. She was a broken girl, hanging by a thread. She wasn't that much different from Blair. She has everything on the tip of her finger but somehow, he felt as if Serena didn't want any of that. But she was living with, with her luck that seems to make her sad. Her luck that took away a family that she wanted.

Suddenly Serena knocked down her glass and passed out. She was drinking too much. Dan pulled her arm around his shoulder, now literally escorting her out of the bar. It was loud and it was blurry, no one noticed the drunk Serena, or maybe just maybe, they had seen it too much. Dan hailed a cab but seems like everyone decided to take a cab today.

"Shit," Dan cursed under his breath. Cece would totally kill him if something happened to Serena. "Come on."

Suddenly a car pulled over in front of him and the backseat window was pulled down. He knew it would be her somehow.

"Get in," she said slowly and Dan did.

Serena passed out on his lap and he could only look out of the window. It was an awkward situation sitting in a car with your ex and her best friend sleeping on your lap.

"Tell Cece she'll be sleeping at my house for tonight," Blair spoke up after a painfully long silence.

"Yeah," he answered. He wanted to say something, but nothing comes out. It seems that his boost to tell her everything was dampened by the existence of the hierarchy nowadays. And the fact that the debutante ball that he didn't understood shows how maybe he really was making reckless decisions yet again. It was never his thing, but it was Blair's deep roots. He can accept that but he hates how it shows that they have such different social hierarchy.

He carried Serena on his back to Blair's penthouse and he realized it never really did change. The furniture, the scent, the feeling of antique. He puts Serena in the guestroom and closed the door, catching his breathe a bit.

"Here," he sees a small hand giving him a glass of water and there was a young child looking up to him.

"Thanks," he took it and behind the small girl he sees the person that he had always seen prepping Blair, worrying for her and caring for her deeply. "Hey Dorota. Long time no see."

Dorota smiled and as the friendly maid she is, she immediately hugged him tight. "I'm glad you came by Mr. Dan."

Dan laughed a bit and he looked down at the young girl again. "Yours?"

"Oh where are my manners. This is Annabelle, my daughter," Dorota held her daughter in her arms. "This Annabelle, is my very good friend, Mr. Dan."

"He is handsome," Annabelle said in her small voice. Dan smiled.

"Very yes Annabelle. Miss Blair did a good job no?" Dorota said.

"Oh no, I'm not…" Dan was flustered somehow.

"I know you're not, but you will. I have this feeling," Dorota smiled. She touches his arm, soothing it like a mother would. "She might take awhile but she'll get there."

"Dorota, we're not in high school anymore. And it is different now…"

"Then why are you here?" he heard her asking as she walked down the stairs. He looked back and he sees her face, demanding for an answer. "Why are you here?"

Dorota excused herself, leaving Dan with Blair alone.

"I'm…" Dan didn't really know. He impulsively took Cece's offer and decided to show Blair something, but now he wasn't sure what it was. "I'm escorting Serena to the Cotillion."

"Yes I see that," Blair wasn't too happy about it. "If you think toying with Serena would make me think twice about my decisions, well you have mistaken. I am not backing away."

"I am not toying with Serena. Cece specifically asked me to escort Serena, so I can…" he realized that this sounded stupid. "So I can learn a bit about the Upper East Side."

"Why would you want to learn about the Upper East Side. You are from Brooklyn," she defended. He can see her building her walls. He wanted to crush it down but decided against it.

"I am writing Cece's biography and I know I am a judgmental prick. And the best writing method is to go through the subject's life and well, here I am," he didn't insert the fact that she was one of the main reasons on why he took the offer.

"Oh," she seemed disappointed. She looked down and he sees her crossing her arms. "Well, learn anything interesting?"

He wasn't sure where would this be going. "Um, everyone likes drinking and perhaps…" he did learn something from Serena. "Everyone has their own problems and sometimes, you can't really judge the m for it." And it hits back at him and that these things that he is doing, everything he's done was judging Blair. By her choices and by her understanding. He never understood why Blair did what she did, he just judged her and he realized, he was at fault there. He tried to push his believe on her, when she walked away. He never fought for her, just slowly watching. Maybe he didn't have the courage like Blair did, to make a decision, so scared of what is to come. If anything, he was the one comfortable in his own spot, too comfortable to notice that it is draining him.

He didn't realize that he was staring at her. She coughed.

"I think it is late and you probably should go," she looked away.

Blair walked to the elevator with Dan and he seemed dumbfounded. Not until the door was almost closing, on her, maybe forever, he decided to have courage now, and some faith.

"I'm sorry," Dan said slowly. Blair looked up. "I didn't mean to." It could be anything but she somehow figured it out by the sudden warm smile on her lips. Before the elevator door closed again, he goes for it. "Coffee."

"What?" Blair was confused.

"Just a coffee between two people where the girl is a journalist and the guy is some pretentious assoholic writer," Dan hoped for a good answer. He was so afraid she would say no, and would again walk out of his life. And maybe finally he will have to walk out of her life. "I promise you it would also have good conversations."

Blair smiled. "Maybe some other time."

The door closes and even if it was not a yes, it was definitely a no. In a way, he is crawling back in slowly. He sighed. He needs to fight for her more. It will be exhausting but it will be worth it. He went out with a million ways to get back to Blair, to understand her and to tell her that he can be with her as well as she can with him.

Dan walked out of Blair's building, unnoticed by anyone but the guard and a man in suits inside a car. The man watched as Dan hailed a cab and left. Nate Archibald who is in sweatpants and a hoodie walked out of the same building and entered the man's car.

"I saw Blair going up," the man said.

"Really?" Nate huffed. "Must have missed her. Jeez my mum didn't understand that comfy is a trend nowadays."

"I don't see it."

"Well you do wear your tie well," Nate looked at his friend. "Chuck."

**To Be Continued**

**Yes there will be more Derena interactions and yes there will be Chuck being Chuck. Hope you enjoy.**


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